3-tert-butyl-1-(4-nitrophenyl)-1H-pyrazol-5-amine → Hydrochloric Acid

HRID 1174849Notes

Reaction equation

HRID 1174849 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([NH2:19])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([N+]([O-])=O)=[CH:12][CH:11]=2)[N:9]=1)([CH3:4])([CH3:3])[CH3:2].[ClH:20].[CH2:21]([O:23][C:24](=[O:34])[CH2:25]C1C=CC(NN)=CC=1)[CH3:22]>>[ClH:20].[CH2:21]([O:23][C:24](=[O:34])[CH2:25][C:13]1[CH:14]=[CH:15][C:10]([N:8]2[C:7]([NH2:19])=[CH:6][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[N:9]2)=[CH:11][CH:12]=1)[CH3:22].[ClH:20]

Participants

4

Reactant 2

HCID 13023603-tert-butyl-1-(4-nitrophenyl)-1H-pyrazol-5-amineHCID 21254104Ethyl (4-hydrazinophenyl)acetate hydrochloride

Product 2

HCID 313Hydrochloric AcidHCID 86622904ethyl[4-(5-amino-3-tert-butyl-1H-pyrazol-1-yl)phenyl]acetate hydrochloride

Procedure

The title compound was prepared in the same manner as described for 5-tert-butyl-2-(4-nitro-phenyl)-2H-pyrazol-3-ylamine, replacing 4-nitrophenylhydrazine with ethyl(4-hydrazinophenyl)acetate hydrochloride (11.98 g, 51.9 mmol). The title compound was obtained as a white solid (HCl salt, 11.95 g) in 68% yield. 1H-NMR (DMSO-d6) δ 7.52 (d, J=8.4 Hz, 2H), 7.45 (d, J=8.1 Hz, 2H), 5.59 (s, 1H), 4.08 (q, J=7.1 Hz, 2H), 3.77 (s, 2H), 1.27 (s, 9H), 1.20 (t, J=7.1 Hz, 3H); MS LC-MS [M+H]+=302.3, RT=2.44 min.

Workup

  1. customThe title compound was prepared in the same manner

Sources & evidence

ORD record
ord-89d0dfe41b9c49f4a8efe94aab3bc4c1
Source dataset
uspto-grants-2010_11
Patent number
US07838524B2

Reaction notes

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